# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_wj_6_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1829909'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
9-acetylanthracene-tetrafluoroterephthalonitrile
_chemical_name_common            9ACA-TFP
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H12 O), C8 N2 F4'
_chemical_formula_sum            'C40 H24 F4 N2 O2'
_chemical_formula_weight         640.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6109(4)
_cell_length_b                   10.4279(4)
_cell_length_c                   13.0037(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.0520(10)
_cell_angle_gamma                90
_cell_volume                     1568.34(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    199(2)
_cell_measurement_reflns_used    6948
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      119
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18354
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.984
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3836
_reflns_number_gt                2254
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.4243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3836
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.53502(16) 0.4802(2) 0.40313(15) 0.0604(5) Uani 1 1 d . . . . .
C2 C 0.50395(17) 0.5999(2) 0.43250(15) 0.0625(5) Uani 1 1 d . . . . .
C3 C 0.46813(16) 0.62187(19) 0.53003(16) 0.0600(5) Uani 1 1 d . . . . .
C4 C 0.4359(2) 0.7486(3) 0.5615(2) 0.0792(7) Uani 1 1 d . . . . .
C5 C 0.15669(15) 0.60364(18) 0.45491(14) 0.0526(5) Uani 1 1 d . . . . .
C6 C 0.14070(18) 0.7190(2) 0.39558(18) 0.0689(6) Uani 1 1 d . . . . .
H6 H 0.1543 0.7178 0.3246 0.083 Uiso 1 1 calc R U . . .
C7 C 0.1068(2) 0.8291(2) 0.4380(2) 0.0840(7) Uani 1 1 d . . . . .
H7 H 0.0970 0.9042 0.3968 0.101 Uiso 1 1 calc R U . . .
C8 C 0.0856(2) 0.8338(2) 0.5425(2) 0.0872(8) Uani 1 1 d . . . . .
H8 H 0.0609 0.9118 0.5711 0.105 Uiso 1 1 calc R U . . .
C9 C 0.10012(19) 0.7287(2) 0.60278(19) 0.0747(6) Uani 1 1 d . . . . .
H9 H 0.0869 0.7343 0.6737 0.090 Uiso 1 1 calc R U . . .
C10 C 0.13507(15) 0.60870(19) 0.56173(15) 0.0561(5) Uani 1 1 d . . . . .
C11 C 0.14861(17) 0.4978(2) 0.62077(15) 0.0610(5) Uani 1 1 d . . . . .
H11 H 0.1340 0.5016 0.6914 0.073 Uiso 1 1 calc R U . . .
C12 C 0.18262(16) 0.38204(19) 0.58078(14) 0.0558(5) Uani 1 1 d . . . . .
C13 C 0.19700(19) 0.2685(2) 0.64173(18) 0.0737(6) Uani 1 1 d . . . . .
H13 H 0.1820 0.2713 0.7123 0.088 Uiso 1 1 calc R U . . .
C14 C 0.2314(2) 0.1575(2) 0.6014(2) 0.0847(7) Uani 1 1 d . . . . .
H14 H 0.2404 0.0831 0.6435 0.102 Uiso 1 1 calc R U . . .
C15 C 0.2540(2) 0.1515(2) 0.4975(2) 0.0844(7) Uani 1 1 d . . . . .
H15 H 0.2784 0.0726 0.4700 0.101 Uiso 1 1 calc R U . . .
C16 C 0.24158(19) 0.2556(2) 0.43563(17) 0.0684(6) Uani 1 1 d . . . . .
H16 H 0.2573 0.2487 0.3654 0.082 Uiso 1 1 calc R U . . .
C17 C 0.20519(15) 0.37610(18) 0.47418(14) 0.0522(5) Uani 1 1 d . . . . .
C18 C 0.19171(15) 0.48744(18) 0.41386(13) 0.0501(4) Uani 1 1 d . . . . .
C19 C 0.21579(18) 0.4820(2) 0.30188(15) 0.0603(5) Uani 1 1 d . . . . .
C20 C 0.1222(2) 0.4367(3) 0.22600(17) 0.0962(9) Uani 1 1 d . . . . .
H20A H 0.0622 0.5026 0.2164 0.144 Uiso 1 1 calc R U . . .
H20B H 0.0887 0.3578 0.2514 0.144 Uiso 1 1 calc R U . . .
H20C H 0.1539 0.4195 0.1599 0.144 Uiso 1 1 calc R U . . .
F1 F 0.56819(11) 0.46179(14) 0.30840(9) 0.0877(5) Uani 1 1 d . . . . .
F2 F 0.50741(13) 0.69758(13) 0.36700(11) 0.0923(5) Uani 1 1 d . . . . .
N1 N 0.4104(2) 0.8472(2) 0.5883(2) 0.1112(8) Uani 1 1 d . . . . .
O1 O 0.30633(14) 0.5167(2) 0.27400(12) 0.1029(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.336(2) . ?
C1 C2 1.363(3) . ?
C1 C3 1.377(3) 3_666 ?
C2 F2 1.331(2) . ?
C2 C3 1.388(3) . ?
C3 C1 1.377(3) 3_666 ?
C3 C4 1.442(3) . ?
C4 N1 1.134(3) . ?
C5 C18 1.399(3) . ?
C5 C6 1.432(3) . ?
C5 C10 1.434(3) . ?
C6 C7 1.348(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.349(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.433(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.426(3) . ?
C12 C17 1.435(3) . ?
C13 C14 1.346(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.400(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.352(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.430(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.402(3) . ?
C18 C19 1.508(3) . ?
C19 O1 1.198(2) . ?
C19 C20 1.479(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 119.65(19) . . ?
F1 C1 C3 119.77(19) . 3_666 ?
C2 C1 C3 120.57(19) . 3_666 ?
F2 C2 C1 119.87(19) . . ?
F2 C2 C3 119.1(2) . . ?
C1 C2 C3 121.02(18) . . ?
C1 C3 C2 118.41(19) 3_666 . ?
C1 C3 C4 120.5(2) 3_666 . ?
C2 C3 C4 121.1(2) . . ?
N1 C4 C3 178.5(3) . . ?
C18 C5 C6 123.37(18) . . ?
C18 C5 C10 118.89(17) . . ?
C6 C5 C10 117.74(18) . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 122.86(19) . . ?
C11 C10 C5 118.94(17) . . ?
C9 C10 C5 118.20(19) . . ?
C12 C11 C10 122.67(17) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 122.54(19) . . ?
C11 C12 C17 118.85(17) . . ?
C13 C12 C17 118.60(19) . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 121.1(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 123.59(17) . . ?
C18 C17 C12 118.93(17) . . ?
C16 C17 C12 117.47(18) . . ?
C5 C18 C17 121.72(16) . . ?
C5 C18 C19 119.06(17) . . ?
C17 C18 C19 119.22(17) . . ?
O1 C19 C20 120.47(19) . . ?
O1 C19 C18 121.56(18) . . ?
C20 C19 C18 117.94(18) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032


_chemical_properties_physical    Deliquescent
_exptl_crystal_preparation       Luminescent
